I have checked a bag on every flight I have ever taken and now as a 3m miler on AA and 1m miler on Delta, I have learned a thing or two about bag claims. I have experienced liquids emptying out. I would recommend not carrying excess or large volume liquids, just for the bag check cutoff rule...or be prepared to throw everything over 3oz in the trash when you have no choice but to take your bag on board. I would recommend luggage size (currently 62" total H+W+L) that can be taken on board. I would recommend learning to pack less than 50lbs per bag. I would recommend even with small containers, no pop off caps, only screw on caps, otherwise pressure changes will cause leaks. This would apply even to containers taken on board. I would recommend not even coming close to the bag weight limit, only because you may want to bring home souvenirs or a bottle of wine you bought which will now exceed the weight limit. I pack a plastic laundry bag in my checked bag to reuse every trip for dirty laundry. In a pinch, if I exceed the weight limit, it can be used as a small carryon with enough weighty non liquid items (books, shoes, whatever) to reduce the weight. I don't think Delta did anything wrong, and I not aware of any bag damage compensation for damage that occurred inside the bag. You would be lucky if Delta helps on that. Delta has paid me full replacement value for one bag. AA has sent me the same brand and size of luggage they destroyed twice, so I have had experience with claims. Delta allowed you to proceed when you missed the checked bag deadline. They were being very graceful, the reason for your lateness is not relevant. Try checking a oversize bag at O'hare within 45 min of departure time and you will get not get on your scheduled flight, no matter the reason.